If you want the most essential record reflecting Sun Ra's Chicago period during the 1950s, THIS IS IT. Recorded in Chicago in 1958 or 1959, Jazz In Silhouette essentially closes Sun Ra's bebop/hard-bop periods, as his interstellar traveler persona began to vividly evolve in the early 1960s. Once he moved to New York in 1961, he began to explore more adventurous musical terrain.

Jazz In Silhouette opens with the Ra composition “Enlightment” (which also appears on the album Sound Sun Pleasure, which wasn't issued until 1970; all tracks from both albums were recorded at the same sessions). “Enlightment” would remain a staple in Arkestra concerts for the rest of Sunny's life. “Saturn,” “Velvet,” “Horoscope,” “Images (In A Mirror),” and “Blues At Midnight” showcase tenor saxophonist John Gilmore and the rest of the band taking straightforward, but inventive hard-bop solos. "Horoscope" is credited to pianist Mary Lou Williams (a big influence on Sunny), from her 1945 “Zodiac Suite.” On the album closer, an extended “Blues At Midnight,” each horn soloist stretches out as in a live club performance.

On Jazz in Silhouette, Sun Ra and the band radiate the period's Chicago jazz sound, with lilting melodies, intertwining chords, and surprising dynamic shifts. Sunny's compositions demonstrate his ability to write memorable songs in the jazz tradition. As evidenced by the arrangements, at this point in his career Sunny is already somewhat "out there," but it wasn't until he reached New York that he became completely untethered.